LOL

Yes, I know you think LOL means "laughing out loud," and you're correct; it does mean that. But it meant something else originally.

LOL was popularized by San Francisco Chronicle columnist Herb Caen in the 1960s. Caen loved using his own shorthand, and LOL was his go-to for “little old lady.” 

 His 1960 book Only in San Francisco contained a description of an outfit that included a tricorn hat topped with an “evil-looking bird of prey” that he said was the “regalia of the authentic LOL.” That usage lasted for a few decades.

In 1964, Jan and Dean had a hit with “The Little Old Lady From Pasadena”:
"And everybody’s sayin’ that there’s nobody meaner
than the little old lady from Pasadena.
She drives real fast, and she drives real hard.
She’s the terror of Colorado Boulevard."

As we move into the early 1980s, if you logged into a pre-internet chat system called Viewline, you might have witnessed history. One of its regulars, Wayne Pearson of Calgary, was chatting when someone said something so funny he was embarrassed to be laughing alone in his house. As he told the Calgary Herald years later: “You used to just type ‘hahaha’ really fast so that you would let them know that was very funny in a timely manner, but whatever he had said, it had me bursting out laughing almost to the embarrassment of doing so in a house by myself sitting at a computer.” So he didn’t type hahaha. He typed LOL. Then he had to explain what he meant. 

Viewline is also reportedly where “ROFL” — rolling on the floor laughing — was coined, though there’s no digital archive to prove it. Online shorthand became a thing and continues today.

The first verified instance we have in print came in 1989, in the newsletter for FidoNet, the bulletin-board network that, amazingly, still exists. There it appeared alongside two other classics we still use today: BRB (be right back) and BTW (by the way). 

In 2011, "LOL” was added to the Oxford English Dictionary. Four years later, in 2015, the OED named 😂 — the Face With Tears of Joy emoji — its Word of the Year. We had officially moved from typing our laughter to just sending a face.